Water → ADONA
Reaction equation
[OH2:1].[C-]#N.[K+].[C:5](=[C:8]([O:10][C:11]([C:14]([C:17]([O:20][C:21]([F:24])([F:23])[F:22])([F:19])[F:18])([F:16])[F:15])([F:13])[F:12])[F:9])([F:7])[F:6].OS(O)(=O)=O.COCC[O:34][CH3:35]>>[C:35]([C:5]([CH:8]([O:10][C:11]([C:14]([C:17]([O:20][C:21]([F:22])([F:23])[F:24])([F:18])[F:19])([F:16])[F:15])([F:13])[F:12])[F:9])([F:7])[F:6])([OH:34])=[O:1]Participants
6
Conditions
- Temperature
- 50 °C
Procedure
A mixture consisting of 120 ml H2O, 250 ml ethyleneglycol dimethylether and 26.3 g KCN was heated to 50° C. 110 g MV31 (CF2═CF—O—(CF2)3—O—CF3) were added to the mixture over a period of 35 min. During the addition of MV31 the temperature of the reaction mixture rose to 57° C. The reaction mixture was cooled down to 25° C. before 55 ml concentrated H2SO4 were added. The bottom phase was collected and washed with water. Afterwards, the organic phase was mixed with the same volume of conc. H2SO4 and agitated for 1 h at room temperature. Distillation from the reaction mixture yielded HOOC—CF2—CHF—O—(CF2)3—O—CF3 (overall yield 89%).
Workup
- additionDuring the addition of MV31 the temperature of the reaction mixture
- customrose to 57° C
- additionwere added
- customThe bottom phase was collected
- washwashed with water
- additionAfterwards, the organic phase was mixed with the same volume of conc. H2SO4
- distillationDistillation from the reaction mixture
Sources & evidence
- ORD record
- ord-9410b5a3d5b549b1b2dbe452f07e96d2
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633328B2
Reaction notes
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